Water insoluble azo dyestuffs and fiber dyed therewith



Patented Oct. 12, 1943 UNEED STATES PATENT OFFICE l/VATER INSOLUBLE AZO DYESTUFFS AND FIBER DYED THEREWITH Norbert Steiger and Fred Haarde, Lock Haven, Pa., assignors to American Aniline Products, Inc., New York, N. Y., a corporation of New York No Drawing. Application February 5, 1942, Serial No. 429,650

10 Claims.

cine 0.ono oNHG-QNH-C o-on-o CH3 l x x BEN-Qlialogen L 5H5 C 6H5 i eHs N=N Halogen HzN Halogen with diacetoacetylarylides of the general formula- OHa-CQCHa-OO-NHQQNH-O O-CHz-C O-CHa wherein X represents hydrogen or methyl group.

The dyestufi made, for instance, by coupling the diazo compound from 2 amino-5 chlor diphenyl with diacetoacetyl-O-tolidine on the fiber produces a beautiful, bright greenish yellow shade unexcelled by any other practically used base in combination with this widely employed yellow naphthol.

The following example is given by way of illustration but not in limitation of the invention:

Well boiled and dried cotton yarn is impregnated with a solution per liter 10 grams of diacetoacetyl-O-tolidine, 10 cc. caustic soda solution (38%) and 12.5 cc. of the solvent known by commercial name Cellosolve (ethylene glycol monoethyl ether). The solution is then Well centrifuged.

Then without being dried, the cotton goods is treated with a solution containing per liter the stable salt of the diazo compound of, 2.04 grams of 2 amino-5 chlor diphenyl. It is then well rinsed and soaped.

In this manner there is obtained on the fiber the dyestufi of the formula- The dyestufi dyes a beautiful, bright greenish yellow of very good fastness to light, washing, peroxide, chlorine, and open kier boil.

If diacetoacetyl-benzidine is used instead of diacetoacetyl-O-tolidine, a very bright greenish yellow of very good 'fastness is obtained. In this case the shade of the yellow dyestufi is greener than if the O-tolidine derivative is used.

Likewise, instead of the diazo compound of 2 amino-5-chlor diphenyl, the diazo compound of 2 amino 5 bromo diphenyl may be used with diacetoacetylarylides and bright yellow azo dyestuiis are obtained that possess similar properties.

Having thus described our invention, What We claim is:

1. The water-insoluble azo dyestuifs of the following general formula:

0113.0 O-TH-C O-NHQQNH-C o en-o 0-011;

1 X x N: Halogen b/ =N H 1 i... g B 5 CHE-C O-CH-C ONE-OO-NH-C o/-o11-c O-GHa l N=NOC1 s im-O01 l V wherein X means hydrogen or methyl group,

yielding, when produced on the fiber, vivid yellow dyeings of very good fastness properties,

particularly of very good fastness to light and washing.

3. The water-insoluble azo dyestufi of the following formula:

0113.0 O.THO ONEWNH-C 0-CH-C 0-0113 I Ha H3 @901 N=NQO1 0H5 yielding, when produced on the fiber, a bright greenish yellow of very good fastness to light, washing, peroxide, chlorine and open kier boil.

4. The water-insoluble azo dyestuff of the following formula:

omo O-TH-C ONE-OO-NH-O oo11-o O-OHa yielding, when produced on the fiber, a bright greenish yellow of very good fastness properties.

CuHs

5. The water-insoluble azo dyestuffs of the following general formula:

aHa

Cali:

NORBERT STEIGER. FRED HAARDE. 

